Users have found that booking a flight from Canada to Chicago at least 27 days early can save you up to 78% on average compared to booking a flight this week. If booking 27 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 488 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 663 for flights departing within the next 3 days.
Flights from Canada to Chicago lean towards being more expensive in July. Prices are generally better when you fly from Canada to Chicago in January, with the cheapest ticket starting at C$ 242.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.
Fly from
Fly to
Budget
C$ 277 - C$ 489
Route
Depart
Return
Price
Toronto IslandChicago Midway
YTZ - MDW
YTZMDW
Toronto Island
Thu 25/4
Nonstop1h 47m
Chicago Midway
Thu 2/5
Nonstop1h 42m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 25/4
Nonstop1h 54m
Chicago O'Hare Intl
Thu 2/5
Nonstop1h 45m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 17/4
Nonstop1h 55m
Chicago O'Hare Intl
Wed 24/4
Nonstop1h 40m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Tue 7/5
Nonstop1h 54m
Chicago O'Hare Intl
Tue 14/5
Nonstop1h 43m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Thu 4/7
Nonstop1h 54m
Chicago O'Hare Intl
Sun 7/7
Nonstop1h 48m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Wed 17/4
1 stop6h 09m
Chicago O'Hare Intl
Sat 20/4
1 stop8h 11m
Vancouver IntlChicago O'Hare Intl
YVR - ORD
YVRORD
Vancouver Intl
Wed 24/4
1 stop11h 11m
Chicago O'Hare Intl
Wed 1/5
1 stop8h 38m
CalgaryChicago O'Hare Intl
YYC - ORD
YYCORD
Calgary
Fri 6/9
Nonstop3h 27m
Chicago O'Hare Intl
Tue 10/9
Nonstop3h 39m
Toronto Pearson IntlChicago O'Hare Intl
YYZ - ORD
YYZORD
Toronto Pearson Intl
Fri 3/5
1 stop7h 05m
Chicago O'Hare Intl
Mon 6/5
2 stops12h 49m
No data available for this route at this time. Please check back soon.
Overall
Food
Crew
Boarding
Entertainment
Comfort
Reviews
I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose
Overall
Food
Crew
Boarding
Entertainment
Comfort
Reviews
I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose
Overall
Food
Crew
Boarding
Entertainment
Comfort
Reviews
I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose
Overall
Food
Crew
Boarding
Entertainment
Comfort
Reviews
I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose
Overall
Food
Crew
Boarding
Entertainment
Comfort
Reviews
I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose
Overall
Food
Crew
Boarding
Entertainment
Comfort
Reviews
I would have liked flying out of the airport I chose not a different airport. My flight was moved to San Jose
23%of flight departures | Early morningMidnight to 6 am |
---|---|
32%of flight departures | Morning6 am to noon |
41%of flight departures | AfternoonNoon to 6 pm |
4%of flight departures | Evening6 pm to midnight |
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